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Total Synthesis of the Cyclic Peptide Argyrin B
Author(s) -
Ley Steven V.,
Priour Alain
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:23<3995::aid-ejoc3995>3.0.co;2-p
Subject(s) - dehydroalanine , chemistry , cyclic peptide , total synthesis , peptide , natural product , stereochemistry , peptide synthesis , convergent synthesis , combinatorial chemistry , amino acid , biochemistry
The details of the total synthesis of Argyrin B, a natural product with immunosuppressive properties, are reported below. The two most unusual amino acid residues of this cyclic peptide are 4‐methoxytryptophan and dehydroalanine, which were obtained by modifying known synthetic methods. The linear peptide was assembled in a most convergent fashion then cyclisation followed by generation of the sensitive dehydroalanine afforded synthetic Argyrin B ( 1 ). (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)